Solvent-Tuned Supramolecular Assembly of Fluorescent Catechol/Pyrene Amphiphilic Molecules

F. Nador, K. Wnuk, C. Roscini, R. Solorzano, J. Faraudo, D. Ruiz-Molina, F. Novio

Research output: Contribution to journalArticleResearch

3 Citations (Scopus)

Abstract

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim The synthesis and structuration of a novel low-molecular-weight amphiphilic catechol compound is reported. The combination of a hydrophilic tail containing a catechol unit and a pyrene-based hydrophobic head favors solvent-tuned supramolecular assembly. Formation of hollow nanocapsules/vesicles occurs in concentrated solutions of polar protic and nonprotic organic solvents, whereas a fibril-like aggregation process is favored in water, even at low concentrations. The emission properties of the pyrene moiety allow monitoring of the self-assembly process, which could be confirmed by optical and electronic microscopy. In organic solvents and at low concentrations, this compound remains in its nonassembled monomeric form. As the concentration increases, the aggregation containing preassociated pyrene moieties becomes more evident up to a critical micellar concentration, at which vesicle-like structures are formed. In contrast, nanosized twist beltlike fibers are observed in water, even at low concentrations, whereas microplate structures appear at high concentrations. The interactions between molecules in different solvents were studied by using molecular dynamics simulations, which have confirmed different solvent-driven supramolecular interactions.
Original languageEnglish
Pages (from-to)14724-14732
JournalChemistry - A European Journal
Volume24
DOIs
Publication statusPublished - 1 Oct 2018

Keywords

  • catechol
  • fluorescence
  • self-assembly
  • supramolecular chemistry
  • vesicles

Fingerprint Dive into the research topics of 'Solvent-Tuned Supramolecular Assembly of Fluorescent Catechol/Pyrene Amphiphilic Molecules'. Together they form a unique fingerprint.

Cite this